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Vacation rentals in Chesterfield

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Quick stats about vacation rentals in Chesterfield

  • Total vacation rentals

    Explore 130 vacation rentals in Chesterfield

  • Nightly prices starting at

    Chesterfield vacation rentals start at G$6,276 GYD per night before taxes and fees

  • Verified guest reviews

    Over 8,120 verified reviews to help you choose

  • Family-friendly vacation rentals

    70 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    120 of Chesterfield vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Chesterfield rentals

  • 4.8 Average rating

    Chesterfield stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated vacation rentals in Chesterfield

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
Cottage in Chesterfield

Chatsworth Cottage

Situated on the edge of the Peak District Park, this is the ideal base for exploring Derbyshire. The Cottage is situated on Chatsworth Road just 10 minutes drive from the ‘Palace of the Peak District’. A short journey and you will discover other wonders of the Peak at places like Matlock, Bakewell, Castleton and Buxton. The historic market town of Chesterfield and the famous Crooked Spire is just a 20 minute walk down the Brampton Mile where you will find some great places to shop, eat & drink.

ValueFamilyPets

4.93 out of 5 average rating, 346 reviews
Top guest favorite
A spacious outdoor area features a hot tub alongside a wooden pod structure. Stone tiles lead to steps that access the hot tub, while a small table can be seen nearby. Natural greenery borders the patio, providing a serene backdrop.
Home in Chesterfield

Spa Home with Hottub, Sauna Pool Table

Spa home with sauna, hottub, all modern amenities, on the edge of the Peak District and just 5 minutes walk from Chesterfield train station. 1pm check-in. Perfect for all experiences, extra large bedrooms. There is full-sized pool table, BBQ area, Sonos music, log-burner, open-plan kitchen and living areas. Ideal for several families or large group getaways. Prime location allows you to enjoy the Derbyshire countryside whilst being within walking distance of a multitude of cafes, shops and bars.

ValueLocationParks

4.96 out of 5 average rating, 161 reviews
Top guest favorite
The Tower emerges from a lush green landscape, surrounded by tall trees and manicured grass. The building's robust concrete structure is accented by its original window designs, reflecting the natural beauty of the outdoors in a tranquil setting.
Tower in Bolsover

The Tower

The Tower is the perfect romantic high-end getaway for couples who want to get away from it all in a secluded location and fancy just something different. The Tower has recently been converted for use as a holiday let which was previously an unused ancillary building adjacent to The Water Works, an old water treatment plant near Bolsover, converted to domestic use in 2002 and featured on the Channel 4 programme Grand Designs. Available for single night stays. Discounts on 3+ nights bookings.

FamilyLocationAccuracy

5.0 out of 5 average rating, 254 reviews
Guest favorite
A modern, light-filled living area features a gray sectional sofa adorned with colorful, geometric pillows. A simple wall-mounted shelf is visible on the left, and a front door, partially open, allows natural light to enter the space.
Townhouse in Chesterfield

Cheerful 2- Bedroomed Home in Chesterfield.

This beautiful town house is located right on the edge of the Peak District and within walking distance to Chesterfield's iconic Market Town. This 2 bedroomed modern home has everything you need and is the perfect base for visiting all the local attractions Derbyshire has to offer. The locations boasts a 20 min drive to the well loved Peak District. Along with all the wonderful bars, restaurants, gift & coffee shops just a short walk away. Chesterfield's Golf course is just 15min drive away.

ValueLocationGetting around

4.91 out of 5 average rating, 194 reviews
Guest favorite
A charming two-story cottage is presented with a welcoming façade featuring pale pink and cream walls. A quiet street is visible alongside, with a parking space indicated. Lush trees line the road, enhancing the serene environment of the neighborhood.
Townhouse in Chesterfield

Cottage by the Park Chesterfield - Peak district

Our COTTAGE is situated with a PARK on our doorstep and 15 min drive to Baslow in the PEAK DISTRICT . Also within walking distance to Chesterfield town center and Chatsworth road. Only a 15 min walk to bars, restaurants, coffee shops, and local boutique shops on Chatsworth Road. It is a short drive to Chatsworth house, Bakewell, Matlock and many of the delightful areas in the Peak district. Our home is cozy and welcoming! We hope you will choose us for your next visit to the area.

LocationValueHospitality

4.87 out of 5 average rating, 119 reviews
Top guest favorite
Home in Chesterfield

Charming 18th century stone cottage

Tucked away in a peaceful corner of Newbold Village, within its own private courtyard, Carpenters Mews is a beautifully restored circa-1800 cottage. Full of character and charm, it has been thoughtfully furnished throughout. Whether you’re visiting for business, leisure, or a countryside getaway to the nearby stunning Peak District, this delightful two-bedroom home is a perfect base. It is close to all local amenities, providing everything you need for an enjoyable and comfortable stay.

FamilyLocationSleep quality

4.96 out of 5 average rating, 47 reviews
Top guest favorite
A comfortable living area is furnished with a gray sectional sofa and two leather armchairs. A glass coffee table is positioned centrally, and a wooden cabinet stands against the wall, adding storage space. Double doors lead to the outside, allowing natural light to enter.
Home in Chesterfield

The Long Hall 2 bed ground floor annexed apartment

Long Hall has been lovingly converted into a 6-person, ground floor, annexed apartment, within a quiet housing estate, a short distance from the Peak District. Two large double bedrooms, with rainfall shower en-suites, and a large open-plan living area dining and kitchen area and a large, shared enclosed patio and garden area Long Hall suits leisure and tourist staycations, as well as trade or professional workers, who wish for a home from home. SKY Sports and Movies included

ValueFamilyDecor

4.96 out of 5 average rating, 355 reviews
Guest favorite
A light-filled living area features large arched windows that allow natural light to illuminate the space. A cozy sofa is paired with a sleek dining table set for four and complemented by modern seating. Decorative plants add a fresh touch to the inviting ambiance.
Condo in Chesterfield

Spire View | Chesterfield 2 Bedroom Apartment

Relax in style at Spire View, a beautifully renovated first-floor apartment in the heart of Chesterfield. Bright, spacious, and full of character, it offers two double bedrooms, modern comforts, kitchen and bathroom, as well as lovely views of the town’s iconic crooked spire. Perfect for couples, professionals, or small groups exploring the Peak District or working locally. Just a short walk to the train station (10 min) and town centre (5 min). Paid parking nearby from £3.80/24h

ValueFamilyNearby

4.95 out of 5 average rating, 21 reviews
Top guest favorite
Barn in Holymoorside

Charming grade II listed cottage with hot tub

Chander Hill Cottage is a stylish 3-bedroom barn conversion nestled above the village of Holymoorside, on the edge of the Peak District. This cosy cottage is a perfect base for exploring the countryside, with numerous walks from the door and two pubs just a mile away in the village. Relax in our hot tub with stunning views or warm up by the wood burning stove after a winter walk. The enclosed cottage garden has a patio where you can enjoy a BBQ in the summer. Dogs welcome!

LocationValueCleanliness

4.99 out of 5 average rating, 203 reviews
Superhost
The living area features a comfortable gray sofa, accompanied by decorative cushions. A light wooden bookshelf holds various books, while a dining table adorned with a vase of roses occupies the foreground. The space is filled with natural light from nearby windows.
Condo in Chesterfield

The Corner House A-2 Bedroom Town Centre Apartment

A stylish ground-floor apartment in a beautifully converted 1800s home, recently refurbished to a high standard and exclusively used for Airbnb guests. The property features two double bedrooms, a full bathroom plus a separate toilet, and a fully equipped open-plan kitchen/diner with a sofa bed - perfect for relaxing stays. Within walking distance of Chesterfield town centre and train station, with allocated parking for one car.

FamilyValueBiking

4.82 out of 5 average rating, 148 reviews
Top guest favorite
A modern two-story home features a clean white exterior with large windows and a circular accent window. A wooden fence offers privacy to the front yard, which displays a paved pathway leading to the entrance. The sky is partly cloudy, creating a serene backdrop.
Home in Chesterfield

'Rose House' Modern 3 Bedroom Detached House

Located a mile from Chesterfield town centre. The property consists of a large open plan lounge/kitchen, 2 double bedrooms and 1 single room with bunk beds. The garden is south facing and there is private parking. There are a range of bars, cafe's, restaurants and local amenities just a short walk from the property. Chatsworth House, Haddon Hall and Peak District are 15 minutes drive away.

ValueFamilyHiking

4.98 out of 5 average rating, 284 reviews
Guest favorite
The stone facade of the barn conversion is complemented by a charming archway entrance. Lush green plants are positioned around the door, enhancing the inviting appearance. A cobbled pathway leads towards the entrance, framed by carefully landscaped gardens and a clear blue sky overhead.
Cottage in Barlow

Old Barn Conversion close to the Peak District

This beautiful detached barn conversion has been charmingly renovated, retaining and working with many original features where possible. Tastefully furnished to a very good standard throughout, the open-plan living space has a small/compact kitchen area with a combi/microwave oven and hob. Its stunning beamed vaulted ceiling creates a warm and cosy social environment.

ValueFamilyLayout

4.86 out of 5 average rating, 302 reviews

Popular amenities for Chesterfield vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Chesterfield's top sights

The Crooked Spire

20 locals recommend

The Market

7 locals recommend

Einstein's

7 locals recommend

Other great vacation rentals in Chesterfield

Top guest favorite
Bungalow in Brimington

Roundhouse View

ValueLocationAmenities

4.96 out of 5 average rating, 23 reviews
Guest favorite
A cozy living area is presented with a brown sofa adorned with decorative cushions. A wooden coffee table sits in front, complemented by a patterned area rug. A wall-mounted television and a decorative shelf enhance the space, which is warmed by a stove and illuminated by natural light.
Home in Chesterfield

The Beehive

LocationValueCondition

4.9 out of 5 average rating, 96 reviews
Guest favorite
Home in Derbyshire

unique gatehouse in the peak park

FamilyLocationKitchen

4.93 out of 5 average rating, 43 reviews
Superhost
The modern kitchen is equipped with light-colored cabinetry and a wooden countertop. Stainless steel appliances include a gas stove, microwave, and kettle. A stone backsplash adds texture, while a wine rack and dishware are neatly organized. Adequate lighting illuminates the workspace.
Home in Chesterfield

Cosy 2 bed home CHESTERFIELD

LocationFamilyIndoor spaces

4.97 out of 5 average rating, 36 reviews
Superhost
A warm living space is depicted, featuring a beige sofa and a brown recliner chair. A cozy fireplace is visible, with a small dining table in the foreground. Wall decorations include heart-shaped ornaments, and a staircase leads to the upper level.
Home in Chesterfield

A cosy 2 bedroom family friendly living space

LocationValueBiking

4.74 out of 5 average rating, 370 reviews
Superhost
A light-filled living area features a comfortable sectional sofa in soft gray, complemented by decorative pillows. A dark coffee table occupies the center space, while large glass doors open to a private outdoor seating area, enhancing the connection to nature.
Home in Brimington

Blissful Barry’s

FamilyValueQuiet

4.84 out of 5 average rating, 45 reviews
Superhost
A light-filled living room is presented with a dark leather sectional sofa adorned with yellow cushions. A geometric area rug covers the floor, complementing the modern design. A large flat-screen TV is mounted on the wall, and window shades provide adjustable light control.
Condo in Chesterfield

2 Bed Lovely apartment close to City Center & Rail

LocationFamilyLong stay

4.86 out of 5 average rating, 28 reviews
Top guest favorite
Home in Walton

The Cow Shed at Dale House Farm

LocationFamilyAmenities

5.0 out of 5 average rating, 45 reviews

When is the best time to visit Chesterfield?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$22,803 GYDG$23,012 GYDG$24,476 GYDG$25,732 GYDG$25,522 GYDG$26,359 GYDG$23,012 GYDG$24,895 GYDG$21,757 GYDG$23,430 GYDG$22,594 GYDG$23,012 GYD
Avg. temp4°C5°C7°C9°C12°C15°C17°C17°C14°C11°C7°C5°C

Frequently Asked Questions

  • What are the best places to stay in Chesterfield?

    Look for accommodations around the town center, Hasland, or the Brampton area, which have convenient access to shops and local attractions. Neighborhoods near parks may appeal to those seeking a quieter stay.

  • What are the best things to do in Chesterfield with kids?

    Queen’s Park has playgrounds and open spaces, while local museums and swimming pools provide indoor options. Family-friendly events and seasonal activities add variety throughout the year.

  • What are some of the best things to do in Chesterfield?

    Explore outdoor markets, visit the Church of St Mary and All Saints with its iconic spire, and relax in Queen’s Park. The town has museums, cozy cafés, and easy access to countryside trails.

  • How is the weather in Chesterfield?

    Chesterfield experiences cool winters around 35–44°F (2–7°C), and milder summers averaging 54–71°F (12–22°C). Rain is common year-round, so a waterproof jacket is useful most seasons.

  • When is the best time to visit Chesterfield?

    Late spring and summer are often recommended for milder temperatures and longer daylight hours. Autumn brings colorful foliage, while winter is cooler and tends to be wetter.

  • What are the best places to visit in Chesterfield?

    Enjoy the unique Church of St Mary and All Saints, stroll through Queen’s Park, or discover local history at Chesterfield Museum. The outdoor market brings a lively atmosphere on market days.

  • What are some hiking trails in Chesterfield?

    Explore scenic paths in Queen's Park, wander the countryside around the Peak District, or stroll along canal towpaths. These trails provide a blend of nature, parkland, and gentle walking routes.

  • What are some family activities we can do in Chesterfield?

    Explore the play areas in Queen’s Park, visit local museums, or enjoy leisure centers with swimming and sports facilities. Family walks and outdoor events are frequently suggested on weekends.

  • What are some of the best day trip ideas from Chesterfield?

    Visit the countryside around the Peak District, explore historic stately homes, or tour nearby market towns. Nature reserves and heritage attractions are frequently suggested for day excursions.

  • Are there any pet friendly accommodations available in Chesterfield?

    Pet-friendly stays are available in Chesterfield, particularly around residential neighborhoods and near green spaces. Many hosts welcome pets and provide guidance on local dog walks.

  • What are some local tips for visiting Chesterfield?

    Arriving early for market days is frequently suggested, as you’ll find fresh produce and handmade goods. Carrying an umbrella is helpful, and locals often stroll Queen’s Park for relaxation.

  • What is Chesterfield known for?

    Chesterfield is known for its historic crooked church spire, vibrant outdoor markets, and access to the Peak District. The town blends local heritage with countryside appeal.

  • What are the best hidden gems to explore in Chesterfield?

    Wander lesser-known paths around the Chesterfield Canal, discover small galleries, or enjoy tucked-away cafés in Brampton. These spots provide quieter alternatives to main attractions.

  • What are the best foods to try in Chesterfield?

    Chesterfield has traditional pies, locally baked bread, and hearty pub fare. Afternoon tea is frequently suggested, with sweet treats and locally made cakes featured in cafés.

  • What should I bring for a trip to Chesterfield?

    Pack waterproof clothing and comfortable walking shoes, as rain can happen in any season. Layers are useful for changing temperatures, and a camera may help capture historic architecture and scenery.

  • What is the nightlife in Chesterfield like?

    Chesterfield has a mix of traditional pubs, relaxed bars, and venues with live music. The town center and Brampton area are known for welcoming atmospheres and community events.

  • What are the most popular events or festivals in Chesterfield?

    The Chesterfield Market Festival and annual medieval-themed events are often recommended. Seasonal celebrations, including local fairs and arts festivals, mark highlights on the town’s calendar.

  • Are there family friendly vacation rentals in Chesterfield?

    Many rentals in Chesterfield have family-friendly amenities and are located near parks, shopping, or leisure centers. Options often include homes or apartments with spacious layouts.

Destinations to explore